6785-34-8

Usage

InChI:InChI=1/C27H48O6/c1-15(4-7-22(31)16(13-28)14-29)19-5-6-20-25-21(12-24(33)27(19,20)3)26(2)9-8-18(30)10-17(26)11-23(25)32/h15-25,28-33H,4-14H2,1-3H3/t15-,17+,18-,19-,20+,21+,22-,23-,24+,25+,26+,27-/m1/s1

Upstream product

• 1100696-11-4 (24RS,25RS)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate 
• 2097-89-4 cholic acid triformate 
• 74670-08-9 (3α,5β,7α,12α)-3,7,12-tris(formyloxy)cholan-24-oyl chloride 
• 81-25-4 cholic acid 
• 859839-61-5 diethyl 7α,12α-di(formyloxy)-3α,24(R)-dihydroxy-5β-cholestane-26,27-dioate 
• 859839-57-9 diethyl 3α,7α,12α-tri(formyloxy)-24-oxo-5β-cholestane-26,27-dioate 
• 859839-64-8 diethyl 3α,24(R)-bis(tetrahydropyran-2-yloxy)-7α,12α-di(formyloxy)-5β-cholestane-26,27-dioate 
• 119068-78-9 (24R,25S)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate 
• 140851-10-1 (24R,25R)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate 
• 881023-47-8 (24RS,25RS)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sulfonic acid 
• 108-24-7 acetic anhydride 

Relevant academic research and scientific papers

Study on the bile salt, sodium scymnol sulfate, from Lamna distropis. III. The structures of a new sodium scymnol sulfate and new anhydroscymnols

Two sodium scymnol sulfates, 1 and 2, were isolated by two steps of chromatography from the bile of Lamna ditropis. Compound 2 was identified as (24R,25S)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate and the structure of 1 was determined to be (24R,25R)-(+)-3α,7α,12α,24,26-pentahydroxy-5β-cholestan-27-yl sodium sulfate, based on the spectral data and chemical transformations. Based on the physical data, the structures of two new anhydroscymnols, 3 and 4, prepared from 1 by alkaline degradation with aqueous potassium hydroxide, were established as (24R,25R)-(+)-24,26-epoxy-5β-cholestane-3α,7α,12α,27-tetrol and (24R)-(+)-26,27-epoxy-5β-cholestane-3α,7α,12α,24-tetrol, respectively. The other shark bile constituents were also analyzed, and the hydrolysis of the sulfate ester function of 1 and 2 was examined.

A Scalable stereoselective synthesis of scymnol

A high-yielding, stereoselective synthesis of scymnol 1 has been carried out in five steps starting from commercially available cholic acid 2. The synthesis was designed with the aim of eventual large-scale processing. Triformyloxycholic acid chloride 4 was treated with the magnesium enolate of diethyl malonate to afford the β-keto diester, diethyl 3α,7α, 12α-triformyloxy-24-oxo-5β-cholestane-26,27-dioate 5. The key step in the synthesis was the stereoselective hydroganation of β-keto diester 5 to give the corresponding β-hydroxy diester 6 using a BINAP nithenium(n) catalyst. Subsequent reduction of the diester moiety and deprotection of the hydroxyl groups afforded scymnol 1.

On the Synthesis of Scymnol

Reinvestigation of a reported synthesis of scymnol (5β-cholestane-3α,7α,12α,24,26,27-hexol) has cast doubt on the success of that synthetic route.A modified synthetic pathway has been developed and scymnol, racemic at C24, has been unequivocally prepared from cholic acid.Extensive proton and 13C n.m.r. spectroscopy has been used to confirm the strcuture of the product.A new, simple method of desulfation of natural scymnol sulfate has been developed.